Toronto Star
· collected 2026-09-13 · by Matt Brown The Associated Press
Ever since Democrat Kamala Harris lost the presidential election to Donald Trump two years ago, political strategist Khalil Thompson has been traveling the country to figure out why Black men inched toward a white Republican rather than a Black woman.
asserted
men → lose → Republican
Although Black men vote overwhelmingly Democratic, even small shifts in their support can help swing razor-thin elections.
asserted
shifts → vote → elections
They are often some of the most scrutinized but least understood voters, a blind spot that Thompson wants to fix.
asserted
Thompson → scrutinize → that
His mission led him to a Philadelphia barbershop one recent Friday night, where Thompson’s organization, Win With Black Men, organized a conversation that mixed with the sounds of buzzing clippers and a break to eat cheesesteaks.
asserted
that → lead → cheesesteaks
“We know the shop is like our own country club that we come to, so we really just want to start having a conversation about what’s important to us in our community,” Thompson told the few dozen people who were getting their hair cut, sat in chairs lined up around the room or stood wherever they found extra space.
asserted
they → know → space
The two-plus hour discussion, which included local politicians, union leaders, lifelong residents, recent arrivals and a few high schoolers, had immense political stakes.
asserted
which → include → stakes
If Democrats cannot run up their numbers in the city, where Black residents are 40% of the population, it’s much harder for them to win Pennsylvania.
asserted
them → run → Pennsylvania
Democrats face similar tests across the country.
asserted
Democrats → face → country
“I am a middle-class Black man who lives in D.C.
asserted
who → live → D.C.
I have no idea what the various day-in-the-life needs would be of the brother who goes to the Bill Pickett rodeo in Houston, the brother that may work on a peanut farmer in Albany, Georgia, versus the brother that lives in Oakland or one who lives in Detroit and goes to work at a car factory plant,” Thompson later told The Associated Press.
uncertain
Thompson → have → Press
“When you’re polling, messaging, making TV decisions for Black men with one monolithic filter, you’re going to lose a broad swath.”
asserted
you → poll → swath
As the conversation got underway, Thompson raised the key question that he has been pondering: Why didn’t some Black men enthusiastically support Harris, the first Black woman nominated for president by a major political party?
asserted
men → get → party
A heated exchange highlights unanswered questions
One exchange reflected the raucous but familiar debates some Black men have had with each other since Trump’s return to the White House.
asserted
men → highlight → House
Stanley Thigpen, a civil engineer, had a theory about Black men and Trump, who he described as “Big T over in 1600,” a reference to the White House’s address at 1600 Pennsylvania Ave.
asserted
he → have → Ave
Thigpen said he is not a supporter, but “what we fail to realize is Trump has always been a prominent figure in Black culture,” he said.
asserted
he → say → culture
Groans, laughs and objections immediately followed.
asserted
Groans → follow → ?
“I gotta push back on that,” interjected Al Glay, a real estate agent.
asserted
Glay → got → that
“You can’t push back on that!” Thigpen retorted.
asserted
Thigpen → push → that
“Rappers rapped about Trump.”
asserted
Rappers → rap → Trump
Glay recalled Trump’s statements about five Black and Latino teenagers, now sometimes known as the Exonerated Five, who were wrongly accused and convicted of the 1989 rape of a white jogger in New York’s Central Park.
asserted
who → recall → Park
“He was blatantly racist,” he said.
asserted
he → say → ?
“How can you support that?”
asserted
you → support → that
Another man brushed that off.
asserted
man → brush → that
“They’re all racist anyway.”
asserted
They → ’re → ?
“You looked your mom in your face, you looked your aunt in the face,” Glay said.
asserted
Glay → look → face
“You looked everybody in the face, and you saw Kamala, and you voted for the white man?”
asserted
you → look → man
The barbershop then briefly erupted.
asserted
barbershop → erupt → ?
Thompson got his start as an organizer for Democrat Barack Obama’s 2008 presidential campaign.
asserted
Thompson → get → campaign
Thompson co-founded Win With Black Men in 2023 to mobilize Black men and highlight their priorities.
asserted
co → co → priorities
The organization’s efforts were turbocharged after Harris entered the presidential race and concerns spread that Black men wouldn’t enthusiastically back the then-vice president.
Harris visited the same shop — Philly Cuts in West Philadelphia — during her campaign, nine days before she lost to Trump.
asserted
she → turbocharge → Trump
She discussed ways to improve Black male representation in education, including increasing pay and reducing student loans with the local state representative.
asserted
She → discuss → representative
Men debated how to provide role models and educational opportunities for Black youths, whether the city’s food deserts were the result of intentional policy and whether artificial intelligence posed greater risks or rewards for them in the labor market.
asserted
intelligence → debate → market
But all agreed on greater government investment in their communities.
asserted
all → agree → communities
Thompson said he had found that Black men across regions, educational backgrounds and income levels are interested in policies that could help them serve as breadwinners and caregivers, build paths to independent wealth and obtain educational opportunities that boost financial independence and versatility.
uncertain
that → say → independence
Some shared feelings of disillusionment with politics that crossed party lines.
“For the longest time, we always have a reason to distrust government, because we know our history, right?” said Maurice Anderson, one of the barbers.
asserted
Anderson → share → barbers
He remembered that Democratic President Bill Clinton signed legislation that boosted criminal penalties that disproportionately sent Black people to prison.
asserted
that → remember → prison
“What has happened,” he said, “is that we’re tapped out.”
asserted
we → happen → ?
But even that was a trap, he added: “They want you to fall back.”
asserted
you → add → ?
State Sen. Vincent Hughes, a Democrat, acknowledged the disillusionment.
asserted
Hughes → acknowledge → disillusionment
“It’s always important that we’re having dialogue because we’ve got to turn that anger into action,” he said afterward.
asserted
he → ’ → action
…and 17 more, not listed.
